4-(p-Fluoro­benzyl­idene­amino)-3-methyl-4,5-di­hydro-1H-1,2,4-triazol-5-one

The molecule of the title compound, C₁₀H₉FN₄O, is almost planar. In the 1,2,4-triazole moiety, the C=N, C-N and N-N bond lengths are normal. The crystal structure is stabilized by intra- and intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.107
• Data-to-parameter ratio = 19.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

4-(p-Fluorobenzylideneamino)-3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one

Crystal data

C10H9FN4O	F(000) = 456
Mr = 220.21	Dx = 1.415 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.0012 (8) Å	Cell parameters from 8026 reflections
b = 13.8430 (12) Å	θ = 1.5–29.5°
c = 11.1307 (11) Å	µ = 0.11 mm^−1
β = 106.572 (8)°	T = 293 K
V = 1033.95 (18) Å^3	Prismatic, colourless
Z = 4	0.4 × 0.37 × 0.3 mm

Data collection

Stoe IPDS-II diffractometer	1657 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	Rint = 0.000
Plane graphite monochromator	θmax = 29.5°, θmin = 1.5°
Detector resolution: 6.67 pixels mm^-1	h = −9→9
rotation method scans	k = −19→19
10015 measured reflections	l = −15→15
2861 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0664P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.89	(Δ/σ)max < 0.001
2861 reflections	Δρmax = 0.14 e Å^−3
147 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.054 (11)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.09601 (15)	0.55573 (7)	0.16483 (8)	0.0643 (3)
N1	0.17354 (14)	0.41525 (7)	0.28943 (8)	0.0463 (2)
N4	0.22909 (15)	0.44457 (7)	0.41330 (8)	0.0486 (2)
N3	0.10686 (17)	0.30559 (8)	0.13995 (9)	0.0577 (3)
C4	0.21359 (17)	0.53276 (9)	0.43871 (10)	0.0503 (3)
H4	0.1680	0.5777	0.3748	0.060*
C1	0.11110 (18)	0.46737 (9)	0.17835 (10)	0.0500 (3)
N2	0.07382 (18)	0.39789 (8)	0.09126 (9)	0.0596 (3)
H2	0.0330	0.4096	0.0122	0.071*
C3	0.2264 (2)	0.24182 (10)	0.35482 (12)	0.0632 (4)
H3A	0.1855	0.1803	0.3162	0.095*
H3B	0.1631	0.2527	0.4196	0.095*
H3C	0.3684	0.2423	0.3905	0.095*
F1	0.41026 (16)	0.65176 (10)	0.93557 (8)	0.1079 (4)
C5	0.26844 (17)	0.56322 (9)	0.57039 (10)	0.0499 (3)
C2	0.16824 (18)	0.31863 (9)	0.25981 (10)	0.0490 (3)
C6	0.2527 (2)	0.65941 (11)	0.59875 (13)	0.0623 (3)
H6	0.2088	0.7041	0.5344	0.075*
C10	0.3333 (2)	0.49743 (11)	0.66734 (11)	0.0609 (3)
H10	0.3442	0.4324	0.6492	0.073*
C8	0.3644 (2)	0.62288 (14)	0.81434 (12)	0.0714 (4)
C9	0.3819 (2)	0.52754 (13)	0.79032 (12)	0.0721 (4)
H9	0.4258	0.4836	0.8555	0.087*
C7	0.3020 (2)	0.69012 (12)	0.72261 (15)	0.0726 (4)
H7	0.2925	0.7549	0.7422	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0990 (7)	0.0497 (5)	0.0388 (4)	0.0096 (5)	0.0111 (4)	0.0034 (4)
N1	0.0574 (5)	0.0488 (6)	0.0303 (4)	0.0004 (4)	0.0084 (4)	0.0014 (4)
N4	0.0565 (5)	0.0563 (6)	0.0309 (4)	−0.0024 (5)	0.0088 (4)	−0.0006 (4)
N3	0.0790 (7)	0.0508 (6)	0.0408 (5)	0.0026 (5)	0.0130 (5)	0.0002 (4)
C4	0.0586 (7)	0.0556 (7)	0.0351 (5)	−0.0004 (5)	0.0107 (5)	0.0021 (5)
C1	0.0635 (7)	0.0512 (7)	0.0332 (5)	0.0042 (5)	0.0105 (5)	0.0026 (5)
N2	0.0894 (8)	0.0524 (6)	0.0317 (4)	0.0069 (5)	0.0087 (4)	0.0017 (4)
C3	0.0807 (9)	0.0546 (8)	0.0512 (7)	−0.0011 (6)	0.0138 (6)	0.0098 (6)
F1	0.1119 (8)	0.1509 (11)	0.0536 (5)	−0.0215 (7)	0.0118 (5)	−0.0464 (6)
C5	0.0492 (6)	0.0611 (7)	0.0389 (5)	−0.0051 (5)	0.0118 (4)	−0.0039 (5)
C2	0.0580 (7)	0.0478 (7)	0.0399 (6)	−0.0009 (5)	0.0118 (5)	0.0021 (5)
C6	0.0670 (8)	0.0638 (9)	0.0566 (7)	−0.0034 (6)	0.0183 (6)	−0.0069 (6)
C10	0.0698 (8)	0.0688 (9)	0.0403 (6)	−0.0029 (6)	0.0095 (5)	−0.0022 (6)
C8	0.0650 (8)	0.1016 (13)	0.0451 (7)	−0.0171 (8)	0.0114 (6)	−0.0242 (8)
C9	0.0783 (9)	0.0936 (12)	0.0385 (6)	−0.0062 (8)	0.0072 (6)	−0.0033 (7)
C7	0.0741 (9)	0.0754 (10)	0.0705 (9)	−0.0128 (7)	0.0241 (7)	−0.0291 (8)

Geometric parameters (Å, º)

O1—C1	1.2332 (15)	C3—H3B	0.9600
N1—C2	1.3755 (15)	C3—H3C	0.9600
N1—N4	1.3824 (12)	F1—C8	1.3552 (15)
N1—C1	1.3899 (14)	C5—C6	1.3801 (19)
N4—C4	1.2648 (16)	C5—C10	1.3859 (19)
N3—C2	1.2923 (14)	C6—C7	1.3890 (19)
N3—N2	1.3814 (15)	C6—H6	0.9300
C4—C5	1.4671 (15)	C10—C9	1.3775 (18)
C4—H4	0.9300	C10—H10	0.9300
C1—N2	1.3374 (16)	C8—C7	1.358 (2)
N2—H2	0.8600	C8—C9	1.359 (2)
C3—C2	1.4729 (17)	C9—H9	0.9300
C3—H3A	0.9600	C7—H7	0.9300
C2—N1—N4	120.35 (9)	C6—C5—C4	119.38 (12)
C2—N1—C1	108.15 (9)	C10—C5—C4	121.55 (12)
N4—N1—C1	131.48 (10)	N3—C2—N1	111.20 (10)
C4—N4—N1	119.26 (10)	N3—C2—C3	125.65 (12)
C2—N3—N2	104.18 (10)	N1—C2—C3	123.15 (10)
N4—C4—C5	119.09 (11)	C5—C6—C7	120.59 (14)
N4—C4—H4	120.5	C5—C6—H6	119.7
C5—C4—H4	120.5	C7—C6—H6	119.7
O1—C1—N2	129.24 (10)	C9—C10—C5	120.53 (14)
O1—C1—N1	128.15 (10)	C9—C10—H10	119.7
N2—C1—N1	102.61 (10)	C5—C10—H10	119.7
C1—N2—N3	113.87 (10)	F1—C8—C7	118.70 (16)
C1—N2—H2	123.1	F1—C8—C9	118.25 (15)
N3—N2—H2	123.1	C7—C8—C9	123.04 (13)
C2—C3—H3A	109.5	C8—C9—C10	118.61 (14)
C2—C3—H3B	109.5	C8—C9—H9	120.7
H3A—C3—H3B	109.5	C10—C9—H9	120.7
C2—C3—H3C	109.5	C8—C7—C6	118.16 (15)
H3A—C3—H3C	109.5	C8—C7—H7	120.9
H3B—C3—H3C	109.5	C6—C7—H7	120.9
C6—C5—C10	119.06 (12)
C2—N1—N4—C4	−172.87 (11)	N4—N1—C2—N3	177.92 (10)
C1—N1—N4—C4	4.96 (18)	C1—N1—C2—N3	−0.37 (14)
N1—N4—C4—C5	178.63 (10)	N4—N1—C2—C3	−2.17 (18)
C2—N1—C1—O1	−179.62 (13)	C1—N1—C2—C3	179.54 (12)
N4—N1—C1—O1	2.4 (2)	C10—C5—C6—C7	0.3 (2)
C2—N1—C1—N2	−0.10 (13)	C4—C5—C6—C7	179.43 (12)
N4—N1—C1—N2	−178.14 (11)	C6—C5—C10—C9	−0.1 (2)
O1—C1—N2—N3	−179.97 (13)	C4—C5—C10—C9	−179.27 (13)
N1—C1—N2—N3	0.53 (14)	F1—C8—C9—C10	179.25 (13)
C2—N3—N2—C1	−0.76 (15)	C7—C8—C9—C10	−0.3 (2)
N4—C4—C5—C6	179.70 (12)	C5—C10—C9—C8	0.2 (2)
N4—C4—C5—C10	−1.15 (18)	F1—C8—C7—C6	−179.12 (12)
N2—N3—C2—N1	0.66 (14)	C9—C8—C7—C6	0.5 (2)
N2—N3—C2—C3	−179.25 (12)	C5—C6—C7—C8	−0.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.86	1.98	2.832 (1)	172
C3—H3C···F1^ii	0.96	2.45	3.175 (2)	132
C4—H4···O1	0.93	2.27	2.939 (2)	129

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y−1/2, −z+3/2.